Benzathine benzylpenicillin

Benzathine benzylpenicillin
Combination of
Benzylpenicillin	antibiotic
Benzathine	stabilizer
Clinical data
Trade names	Bicillin L-A, Permapen, others
Other names	penicillin benzathine benzyl, benzathine penicillin, penicillin G benzathine, benzylpenicillin benzathine
AHFS/Drugs.com	Professional Drug Facts
License data	US DailyMed: Penicillin G benzathine;
Pregnancy; category	AU: A;
Routes of; administration	Intramuscular injection
ATC code	J01CE08 (WHO) ;
Legal status
Legal status	CA: ℞-only; US: ℞-only;
Identifiers
CAS Number	41372-02-5 ;
PubChem CID	15232;
DrugBank	DB01053 ;
ChemSpider	14498 ;
UNII	RIT82F58GK;
KEGG	D02157 ;
ChEBI	CHEBI:51352 ;
ChEMBL	ChEMBL3989515 ;
E number	E708 (antibiotics)
CompTox Dashboard (EPA)	DTXSID2047804 ;
ECHA InfoCard	100.014.782
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Benzathine benzylpenicillin, also known as benzathine penicillin G (BPG), is an antibiotic medication useful for the treatment of a number of bacterial infections.^[3] Specifically it is used to treat strep throat, diphtheria, syphilis, and yaws.^[3]^[5] It is also used to prevent rheumatic fever.^[5] It is given by injection into a muscle.^[3]^[5] It is known as "Peanut Butter Shot" in US military slang due to its appearance.^[6]

Quick Facts Combination of, Benzylpenicillin ...

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Side effects include allergic reactions including anaphylaxis, and pain at the site of injection.^[5] When used to treat syphilis a reaction known as Jarisch-Herxheimer may occur.^[5] It is not recommended in those with a history of penicillin allergy or those with syphilis involving the nervous system.^[5]^[3] Use during pregnancy is generally safe.^[3] It is in the penicillin and beta lactam class of medications and works via benzylpenicillin.^[3]^[5] The benzathine component slowly releases the penicillin making the combination long acting.^[7]

Benzathine benzylpenicillin was patented in 1950.^[2]^[8] It is on the World Health Organization's List of Essential Medicines.^[9]

It is used to treat strep throat, diphtheria, syphilis, and yaws.^[3]^[5]

Chemopreventive

A single large 1.2-million-unit dose of intramuscular BPG is given to US military recruits. The Army in particular has a policy to inject all recruits if not allergic, though supply issues and individual base choices have reduced the coverage. A retrospective analysis shows that it reduces the rate of all-cause acute respiratory disease by 32% among Army recruits.^[10]

The possible adverse effects are generally similar to other forms of penicillin. BPG is overall well-tolerated, but pain from the injection site is a common concern.^[11]

It is marketed by Pfizer (formerly by Wyeth) under the trade name Bicillin L-A.^[12]

British Pharmacopoeia^[13]

[1]
Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 94. ISBN 9781284057560.
[2]
Engel J, Kleemann A, Kutscher B, Reichert D, eds. (2009). Pharmaceutical Substances: Syntheses, Patents and Applications of the most relevant APIs (5th ed.). Georg Thieme Verlag. p. 134. ISBN 9783131792754. Archived from the original on 20 December 2016.
[3]
"Penicillin G Benzathine (Professional Patient Advice) - Drugs.com". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 10 December 2016.
[4]
"Product monograph brand safety updates". Health Canada. 6 June 2024. Retrieved 8 June 2024.
[5]
World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 98, 104. hdl:10665/44053. ISBN 9789241547659.
[6]
Kirkpatrick T (11 February 2020). "Why the Most Dreaded Injection is Called the 'Peanut Butter' Shot". Military.com. Retrieved 21 December 2021.
[7]
Ebadi M (2007). "Penicillin G". Desk Reference of Clinical Pharmacology (2nd ed.). CRC Press. p. 555. ISBN 9781420047448. Archived from the original on 20 December 2016.
[8]
US patent 2627491, Szabo JL, Bruce WF, "Penicillin salts of substituted alkylene diamines", published 1953-02-03, issued 1953-02-03, assigned to Wyeth LLC and Wyeth Inc
[9]
World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
[10]
Ball JD, Prosperi MA, Brown A, Chen X, Kenah E, Yang Y, et al. (October 2018). "The role of benzathine penicillin G in predicting and preventing all-cause acute respiratory disease in military recruits: 1991-2017". Epidemiology and Infection. 146 (14): 1854–1860. doi:10.1017/S0950268818001838. PMC 9506690. PMID 29974837.
[11]
Gartlan WA, Rahman S, Reti K (2023). "Benzathine Penicillin". StatPearls. StatPearls Publishing. PMID 29939545.
[12]
"Bicillin® L-A" (PDF). US FDA. Retrieved 31 July 2023.
[13]
British Pharmacopoeia Commission Secretariat. "Index (BP 2009)" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 26 March 2010.

[Ric2015-1] [1]
Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 94. ISBN 9781284057560.

[Eng2014-2] [2]
Engel J, Kleemann A, Kutscher B, Reichert D, eds. (2009). Pharmaceutical Substances: Syntheses, Patents and Applications of the most relevant APIs (5th ed.). Georg Thieme Verlag. p. 134. ISBN 9783131792754. Archived from the original on 20 December 2016.

[PPA2016-3] [3]
"Penicillin G Benzathine (Professional Patient Advice) - Drugs.com". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 10 December 2016.

[4] [4]
"Product monograph brand safety updates". Health Canada. 6 June 2024. Retrieved 8 June 2024.

[WHO2008-5] [5]
World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 98, 104. hdl:10665/44053. ISBN 9789241547659.

[Kirkpatrick-6] [6]
Kirkpatrick T (11 February 2020). "Why the Most Dreaded Injection is Called the 'Peanut Butter' Shot". Military.com. Retrieved 21 December 2021.

[7] [7]
Ebadi M (2007). "Penicillin G". Desk Reference of Clinical Pharmacology (2nd ed.). CRC Press. p. 555. ISBN 9781420047448. Archived from the original on 20 December 2016.

[8] [8]
US patent 2627491, Szabo JL, Bruce WF, "Penicillin salts of substituted alkylene diamines", published 1953-02-03, issued 1953-02-03, assigned to Wyeth LLC and Wyeth Inc

[WHO21st-9] [9]
World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[10] [10]
Ball JD, Prosperi MA, Brown A, Chen X, Kenah E, Yang Y, et al. (October 2018). "The role of benzathine penicillin G in predicting and preventing all-cause acute respiratory disease in military recruits: 1991-2017". Epidemiology and Infection. 146 (14): 1854–1860. doi:10.1017/S0950268818001838. PMC 9506690. PMID 29974837.

[11] [11]
Gartlan WA, Rahman S, Reti K (2023). "Benzathine Penicillin". StatPearls. StatPearls Publishing. PMID 29939545.

[FDA-12] [12]
"Bicillin® L-A" (PDF). US FDA. Retrieved 31 July 2023.

[ibp2009-13] [13]
British Pharmacopoeia Commission Secretariat. "Index (BP 2009)" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 26 March 2010.

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Chemopreventive

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Benzathine benzylpenicillin

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Adverse effects

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Compendial status

References